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By strange coincidence, on Friday I finished Umberto Eco’s novel Foucault’s Pendulum and the next day I woke up to the news of his death at 84 years old. I really enjoyed the novel (his second, published in 1988) and wanted to explore my reactions and lessons I drew from it. I’m going to cover real plot spoilers, so don’t read on if that’s not your thing.

The book’s plot follows a narrator, Casaubon, and two of his colleagues at a publishing house where they’ve been publishing books on the occult and similar subjects. As a joke and a lure to attract more of these authors, the protagonists fabricate an elaborate Plan that weaves together many of the crazy threads they find in the manuscripts sent to them. For many years they had mocked the conspiracy theories they found in these manuscripts until finally, with the creation of their own Plan and evidence of murder and death threats regarding it, they begin to believe in it themselves, and it becomes their undoing.

In part, Foucault’s Pendulum is a critique on those who would take history, stories, and literature too seriously in their quest to find connections and interpret hidden reasons and intentions behind events. So it should be with a sense of irony that any of us attempt to read more into Eco’s work, probing beneath the surface, but nonetheless, as we’ll discuss, this kind of process can be very rewarding and is ultimately a key to innovation and the improvement of our real understanding of the world.

The biggest metaphor that runs wholly throughout the novel is that of the pendulum. The pendulum is obviously important on the surface: the novel’s title comes from the invention of Léon Foucault, whose device was the first to demonstrate the earth’s rotation without relying on celestial observation. His instrument is basically a large pendulum, big enough that its path can be easily traced and observed for slight changes as the earth rotates throughout the day. Casaubon, lost in a sea of conspiracy theories and falsehood, fetishizes Foucault’s invention as a demonstration of a fixed point of reference. Wobbling around in the multitude of false connections he and his partners have made, Casaubon longs for the ability to look up and see himself attached to something fixed. Casaubon’s observations reveal the obvious fragments of what Eco is trying to tell us: that we can look for fixed points of truth when lost, that we long for that fixed point in the universe to tell us we’re okay, or that science may hint at where we can find truth and fixed points in life.

But that only scratches the surface! I don’t know of anyone who has really examined all the ways in which you can spot a pendulum operating throughout Eco’s work. There are several in the plot structure alone: from how the first and last few chapters take place in the Conservatoire, with the bulk of the plot in the middle; Casaubon’s time in Brazil, where he escapes from his occult readings, only to be interrupted by a ritual that preempts his return to Milan; as well as Casaubon’s back and forth between his work on the Plan and his relationships and wife’s pregnancy.

Examples of the pendulum throughout the novel Foucault’s Pendulum.

Beyond the concrete plot movements, our protagonists are constantly struggling with the choice between two opposite sides of a pendulum: to believe or disbelieve a theory, to decide whether a claim is truth or conjecture, to trust a surface explanation or seek hidden meaning, and whether to act with bravery or cowardice. For much of the book our heroes swing back and forth between decisions on either side of this spectrum, but inevitably their aggregate choices begin to favor one side, setting them on their spiral towards doom.

Sensing their compounded failure, the protagonists desperately seek an out. It’s here that Eco introduces one of his best jokes in the book and one of the most important semiotic concepts: the power of no.

Early in the book Casaubon attempts to access his colleague’s computer, which is password protected behind the very specific phrase “Do you know the password?” After a few hours of trying the most clever combinations of words and phrases he’s sure his friend would use, out of exasperation Casaubon decides to answer the phrase literally, with NO. This ends up being the password and is a key mirror to the final moments of the book.

The Plan, invented by Casaubon and his colleagues, once heard by the various crazies and devout occultists across Europe, sends these lunatics into a frenzy over getting access to the secret weapon the Plan is said to reveal. In their final moments, as they are interrogated and face murder by these occultist lunatics, the protagonists realize they still have the power to use no. “Do you have the secret location of the weapon?” “No.”

“No” as a source of inertia for getting to the other side of the pendulum.

No is important to Eco for two reasons, the first is its power to restore agency in someone who feels they have no control. Casaubon and friends, in their search for outside sources of truth and reference, decide they must accept any theory or connection, no matter how far fetched. Their personal lives devolve similarly, as they accept whatever happens to them with indifference. It’s only through their rediscovery of rejection and saying no that they realize they can swing back to a position of agency and personal standing. By rejecting the Plan and saying no to the occultist’s query, they are able to reassert their position and identity as non-occultists.

The second way in which no is important to Eco is in how concepts acquire meaning through defining what they are not. This is the via negativa sense, the idea from theology where you attempt to define God by reasoning about what (s)he is not. No is used to disconnect concepts from others, to break connections and to establish boundaries. It’s key to determining which side of the conceptual pendulum you are on.

Eco’s life is a bit of a pendulum in its own right: his writings go back-and-forth between academic publications and popular fiction. If we leave the world of Casaubon and look to Eco’s work in semiotics, we quickly find references to the same challenges he presents in the novel.

In his chapter of the book The Sign of Three, Eco delves into the various processes of abduction. Abduction is likened to the process of hypothesizing, or guessing, about the cause of an event after one has observed the result. When working in a process of abduction, you entertain possible worlds that may differ from experience: “…abductions… are world-creating devices” (pg 214).

Eco goes on to give examples of the detective or scientist that operate through abduction, highlighting the different incentives for each in their respective domains. The homicide detective, in trying to find who-dun-it, is able to entertain a wide variety of hypotheses in their process of finding the killer. We encourage detectives to consider and not overlook any possible suspect or explanation.

In contrast, scientists may find a very different tolerance for conjecture in their domain. The further their theories deviate from accepted dogma, the more they’ll find difficulty in funding their theories. Science and human progress depends on radical new ideas, but it can be very hard to determine when it’s a good bet and worth proving out.

“Scientific discoveries, medical and criminal detections, historical reconstructions… are all cases of conjectural thinking.” (The Sign of Three, pg 205)

Eco doesn’t paint much of the bright side of conjecturing and world-creation in Foucault’s Pendulum. But we find elsewhere in his work the nod towards the benefits of this process, especially for those at the boundary of some important field or line of inquiry.

Progress everywhere depends on the back-and-forth between truth and conjecture, between hypothesis and verification. If we are to advance our present reality, we must suspend disbelief and entertain alternative worlds. But this is not a one-way process. It requires a delicate balance and teeter-totter, and a consciousness of the consequences.

If you’re a scientist working on a new theory, or an entrepreneur entertaining a new business idea, you would do well to read Foucault’s Pendulum for an instructive lesson in the process and consequences of letting your hypotheses run away from you.

RIP Umberto Eco (1932 – 2016)

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One heuristic we developed at Infochimps and used in several crucial hiring and firing decisions was to ask ourselves “Is this the best job for this person’s career?” Hiring and firing decisions can have a huge impact on an individual, affecting their livelihood and self-perception in significant ways. Once aware of the possible grave effects of hiring a person into the wrong role, or letting someone go, it is really easy for the decision-making process to get all gummed up with emotion and sympathy.

We had a very friendly, people-centered culture at the company. Somehow the initial reasons for letting someone go or passing on a candidate never could add up to the kind of thing you’d want to say to that person’s face. “You don’t fit in here” or “you don’t perform to our standards” can be pretty cold-blooded words to hear, and are not likely to help the individual down their path. We also had a standard we tried to uphold whereby every job candidate left our hiring process with nothing but good things to say (even if we turned them down), same with the folks we had to let go.

One way we found to turn it upside down and come at the problem in as people-centered way as possible, was to ask ourselves “Is this the best job for this person’s career?” Once framed this way, it can be much easier to reach a yes/no decision on your hire/fire dilemma.

As well, many of the issues we might have had or foreseen with this person become helpful points of feedback and ways we could try to set them up for more success down the road:

“You don’t fit in here” becomes “We believe you’ll be happier somewhere else” – Especially in our technology industry, there are hundreds of different companies to choose from for employment, offering a huge variety of cultures that might be more in-line with what that candidate believes in. The latter reasoning makes clear that we don’t want the person to be unhappy in our organization.

“You don’t perform to our standards” becomes “We think you’re earlier in your path than we need for this role, and don’t want to set you up for failure” – This acknowledges their talents and aptitude, and presents the issue in a forward-thinking, optimistic point of view. Instead of “these are the things you lack” it is “these are the things you have yet to learn or acquire.”

In times of a pivot or when money is tight, “we don’t need your job anymore” or “we can’t afford you anymore” are generally neutral and non-personal explanations anyway, but these can be taken another step further and phrased as “we can no longer offer you the kind of role and challenges that would help you grow.” Again, the spirit is that the person will move on to bigger and better things as a result of this.

When a choice is murky because there are two candidates, one with a lot of experience and another with less, asking yourself whether the position is a better next step for either candidate can help narrow the choice. Maybe the more experienced candidate will find the position more humdrum and same-old, not bringing the attitude and excitement you might hope for. Maybe they are excited and consider this a great leap for themselves – but because it’s a new industry or technology area, not because it’s a title bump.

There can be lots of ways to phrase the feedback to a candidate you pass on or someone you let go, none are perfect in every case. I have found, however, that by simply asking the question you put yourself in the frame of mind that yields much more empathetic and helpful discussions about the decision. Next time you have trouble deciding whether to hire a particular candidate or whether to let someone go, try it. Ask yourself: “Is this the best job for this person’s career?”

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Conviction, of choice and reason, has been one of the hardest qualities of good leadership for me to develop. An appreciative and empathetic mind can usually find multiple angles from which to appreciate a story, which makes it hard to call someone or something clearly wrong. Usually if you’ve entered the mind of the other party or explored enough angles, you recognize why the other story may make sense.

Somewhere, there is a line to make between being overly empathetic and a fear of being human – of experiencing guilt. Hanging up on a decision is a key way to flame out as a leader. In such a case you become no more than an invisible man, someone who refuses to run the risk of their own humanity.

There can be ways around this. One of my favorite anecdotes is from Zizek’s story about suicide bombers and their own belief process. In how he tells it, the suicide bomber isn’t as convinced of their cause as we think they are before they commit their act. All the way up to it they have doubt weighing on their mind, and it’s only through the act of the suicide that they prove it to themselves that they were actually committed to the cause.

Empathy can muddy the waters in a way that becomes entrenching and ambiguous. You reach a point over time where you are mired in cognitive dissonance – balancing two opposing mindsets at the same time. Recently I discovered a possible out to this process.

Picture the mind of a suicide bomber just before he blows himself up. Do you really think it’s very different than your own at this moment, where you have been teetering over a choice for the last hour or even days? The severity of his choice is greater than your own, but this is precisely why we shouldn’t expect him to have any easier time convincing himself this is the right course of action. Where your choice is between sticking to your diet for your upcoming birthday dinner, he is erasing himself from his family and culture, all with the aim of serving his country or cause.

If a person in that situation can commit themselves to an action so severe, while you, with your decades of education and first world dilemmas, deliberate back and forth over some inconsequential matter, how does that reflect on yourself?

The example is important because I think it points to a very special mechanism you have to develop if you’re going to be a leader. You have to have a “suicide button” for yourself, a button that says you’ve committed to something with absolutely no regard for the consequences of it to yourself. In fact, you might as well look at the consequences in the same light – certain death. This becomes like the Stoic practice of negative visualization. The worst thing that can happen is that you are destroyed. If you’re prepared for this in light of the choice and the possible benefits for you and the organization, you might just have the conviction needed to carry the group through.

The suicide button is a model for yourself to use against the back-and-forth. For the bomber, hitting his button is actually the final note by which he convinces himself that he is indeed a believer in the cause.

Where leadership depends so much on a vision-driver, a person who holds the accountability stick, you have to be very sure of your decisions and the ultimate success of your organization, even against overwhelming evidence to the contrary. Your job is to know when and where you must push your suicide button and just dive in.

In a remarkable irony, I originally wrote this draft post several years ago and shied away from publishing for whatever reason, probably based in fear/embarrassment. I’m just now coming back out of blog hiding, hoping nor to repeat that pattern.

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For the last year, I’ve gotten an hour-long massage at least once per month. Massage is a hard thing not to love for its own sake, but what’s been interesting is to understand the science behind why massage works. It’s ultimately a process that requires the assistance of outside forces – something or someone presses on your body to enact some change. “Deep tissue” massage is the type of massage I am talking about, which does not mean massage that involves lots of manual strength, but any massage that focuses on affecting structural changes in the body.

One of the leading theories behind massage and why it works involves the formation of fascia, or connective tissue, throughout the body in response to a process called fibrosis. The patterns of movement and stationary positioning we take on, to whatever extent they deviate from your standard design, encourage the formation of this tissue throughout the body to prop up these alternate poses. You can imagine your muscular tissue and cells working constantly at building bridges and trusses throughout your body at any point in time with the intention of enabling the pose to be held and to take stress off the more actively strained muscles.

The challenge with fascia formation is that these bridges aren’t meant to be permanent. They are going to be much more brittle and will adapt the musculoskeletal system in ways not recommended by the manufacturer. Fibrosis is actually behind many well-known permanent ailments of tissue replacement – scarring, cirrhosis, and Crohn’s disease are all examples of fibrosis taken to the extreme. In each of these cases, death or permanent effects result from a natural process of the body (tissue formation and repair) that gets taken to the extreme without being checked. Deep tissue massage is an outside input to assist in the destruction and collapse of these structures to allow the rest of the body’s structure to build and heal in the right direction, avoiding more permanent pains and cramps due to malformed muscle and tissue buildup.

I like to think about the formation of habits as happening within a similar process needing a similar remedy. A normal human brain will have a natural, healthy course of being that we can generally recognize. Happiness, a kind demeanor, and an ability to focus are all examples of observed effects of a brain operating as any designer or user would encourage it.

It’s the unnatural poses, or trains of thought and habit, that can disrupt the normal operation of a healthy brain through the creation of mental bridges into unhealthy territory. Personal examples for me would be the frequent checking of email and social networks throughout the day. Email responsiveness happens to be a core part of my job, but checking Twitter? While there’s value there the process has manifested a kind of fibrosis that would be difficult to deny of its negative daily effects. The distraction started as a prop against whatever stressful topics I wanted to turn away from and has grown into something of a time-suck and an activity that replaces valuable thought and action time that could be better spent focused on the topics at hand at work.

I’d argue that addiction is a type of extreme fibrosis of the brain. As fascia is built up in the muscles to support a poor structure, an unhealthy drug habit is built up as a replacement for healthier ones. Once at this point, AA’s 12 Step Program is the psychological equivalent to a deep tissue massage. And for less severe habitual build-ups, a check-in with a therapist could be the analogy to regular massages for the healthy re-shaping of mental processes.

Technology of all kinds creates a kind of habitual fibrosis, as well. My dad’s driven his motorhome through 47 states over the last decade, navigating highway and local roads alike with the assistance of his GPS. This tool has saved him a ton of hassle from figuring out routes between cities and the best path to a local restaurant, but has created a kind of dangerous dependence. Anytime a resident tries to give him directions to somewhere they’re quickly stopped and asked if they’ve got the address or cross street, instead. The ubiquity of the GPS and mapping devices frees us from having to learn how to get from Austin to Marfa but displaces the local or tacit knowledge we might hope to acquire during a passing visit.

Stoicism is a kind of active therapy against all kinds of bad mental habit formation. The active caution against the dependence (aka “mental bridge building”) on material things smooths the formation of habit towards a reliance on things you’d expect to be longer lasting and unbreakable by external events. Your reputation, countenance, and rational self become personal bridges that last because of their very nature as intrinsic properties not necessarily dependent on externalities.

For everything else, there’s probably a body massage for that. My own takeaways from the fascia and habit analogy is to recognize when it’s occurring and what effective antidotes could be. Tissue buildup and habit formation generally depend on the external environment for their formation, and may require external stimulus to be broken down once again. So, be mindful and pick the massage therapist or mental therapist, in whatever form, that’s going to work for you.

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We all get nervous before an important event. Maybe you’re fundraising and there’s an important meeting coming up with some potential investors. Maybe you’re young and about to meet somebody important. In these cases there might be some 20% chance that, if you can knock the meeting out of the park, you reach some great outcome. Therefore we get anxious about our chances and obsess over that 20% outcome.

I’ve found that this mis-aligns my thinking. The real probabilities you should be thinking about have nothing to do with the event. You have a 80% chance of being the same company you were before the investor meeting, so how about you focus on that. After you meet this important person, you’ll still come home to yourself, so why aren’t you anxious about that?

So many companies focus on fundraising as an end that they forget the most important thing for getting there – you have to build a fundable company. I do it all the time when I think about how this next meeting or opportunity is going to make all the difference in the world, but I’m kidding myself. I find it’s a lot more calming to focus on the things which have the highest chance of coming about (you’re still yourself), and just as importantly, are things you control.

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Streetlights and Shadows is a book by Gary Klein that takes commonly held maxims for decision making and overturns them, revealing cases where these practices break down. The book’s title comes from the story of the man who went looking for his lost housekeys under a streetlight instead of where he lost them in the shadows – he went for where there was more light. We do the same when we resort to old maxims that only help in ordered situations without realizing we need something different. Klein’s book does an impressive job showing us where these problems occur and he prescribes how we can be more resilient decision makers in these scenarios.

He begins by outlining ten of the most widely held beliefs taught about systems and decision making, and after telling a few stories about each he describes a replacement maxim. The ten claims and their replacements are:

Teaching people procedures helps them perform tasks more skillfully. Replacement: In complex situations people will need judgment skills to follow procedures effectively and go beyond them when necessary.

Decision biases distort our thinking. Replacement: Decision biases reflect our thinking. Rather than discouraging people from using heuristics, we should help them build expertise so they can use their heuristics more effectively.

(Sub-point to 2) Successful decision makers rely on logic and statistics instead of intuition. Replacement: We need to blend systemic analysis and intuition.

To make a decision, generate several options and compare them to pick the best one. Replacement: Good decision makers use their experience to recognize effective options and evaluate them through mental simulation.

We can reduce uncertainty by gathering more information. Too much information can get in our way. Replacement: In complex environments, what we need isn’t the right information but the right way to understand the information we have.

It’s bad to jump to conclusions – wait to see the evidence. Replacement: Speculate, but test your speculations instead of committing to them.

To get people to learn, give them feedback on the consequences of their actions. Replacement: We can’t just give feedback; we have to find ways to make it understandable.

To make sense of a situation, we draw inferences from the data. Replacement: We make sense of data by fitting them into stories and other frames, but the reverse also happens: our frames determine what counts as data.

The starting point for any project is a clear description of the goal. Replacement: When facing wicked problems, we should redefine goals as we try to reach them.

Our plans will succeed more often if we identify the biggest risks and then find ways to eliminate them. Replacement: We should cope with risk in complex situations by relying on resilience engineering rather than attempting to identify and prevent risks.

Leaders can create common ground by assigning roles and setting ground rules in advance. Replacement: All team members are responsible for continually monitoring common ground for breakdowns and repairing the breakdown when necessary.

All of his replacement claims have common themes of adaptability, experience, and expertise winning over stricture, linear thinking, and risk management. I’ve found almost all of his ideas to be directly applicable to running a startup and the challenges of making decisions in that kind of environment. You are constantly in the shadows, with only hints of illumination peeking through.

Some of his replacements are no-brainers on a surface level. Procedures are dangerous and often have glaring holes you may suspect but may not be able to pinpoint. Of course data and your frame for looking at it are equally important, and one would expect that over time and with experience you will be able to make more decisions successfully from intuition alone over careful analysis.

His more subtle examples include statements about goal setting, risk management, and heuristics. These examples are especially applicable to teams of people and early stage projects. It’s nearly impossible to set goals in the beginning of projects when there are so many unknowns. Admitting this, and acknowledging that you will have to discover and revise your goals along the way, let’s you clear your mind of these issues and get back to doing. During the process, if you stay aware, the goals you were looking for will emerge on their own.

An early stage company is essentially a group of people trying to do something together. Each person will have their quirks and challenges that make them difficult to work with. You can tinker with a lot of things in a startup’s early days, but not your founding team and stars. By their nature they will usually add a ton of value, but they are unlikely to change. It’s up to you to build a culture where the erratic geniuses around you can get their work done, while minimizing their disturbances to progress elsewhere. A lot of my job is just supporting systems that create a more resilient environment where these folks can still thrive.

These people are just another kind of risk. Accepting you can’t change or get rid of them is the same as accepting that there are risks you are blind to, that you are in a complex situation where instead of a focus on risk elimination you should focus on risk tolerance. You will never be able to list everything that could go wrong and rat out the issues, so you must create an environment that is robust and resilient against these risks.

Some of the biggest ideas missing from Klein’s book come from war. Although he used a few examples from the modern military to show where local problems occur due to a misguided belief in some of the claims above, he made no mention of Boyd and his work on adaptability and the OODA loop, in which expertise and intuition are the keyholes. Klein even has a diagram of his own that looks like a dumbed down version of the loop.

Clausewitz’ idea of friction also gives us a unique stance from which to appreciate Klein’s work. Friction is a very apt term to use when thinking about startup problems. Acknowledgement of its ever-presence, with the care to combat it using the toolkit Klein provides, just might help us get better at making good decisions in our complex world.